In his first feature, The Target Shoots First, Chris Wilcha documented his tenure at Columbia House, the mail-order music service whose ads famously promised “12 CDs for a penny.” Then a recent NYU philosophy graduate, Wilcha landed the job partly due to his familiarity with “alternative culture,” a burgeoning new market at the time (Nirvana’s In Utero was soon to be released), and brought a sardonic Gen X sensibility to chronicling his time in the company’s marketing department. Part workplace comedy and part personal essay, Target chronicled Wilcha’s anxiety about selling out his personal integrity and punk rock principles by commodifying his generation’s tastes. At the same time, he and equally disaffected, creatively-inclined colleagues tried to mold the system in their own image by turning the company’s sales catalogue into an alternative publication, complete with snarky copy and genuine music criticism. Wilcha’s unfettered access to Columbia House, from the factory floor to company retreats, and unique commentary renders Target a perfect snapshot of ’90s culture and a timeless treatise on rationalizing well-paid, soul-sucking office jobs.

23 years later, Wilcha returns with Flipside, a spiritual sequel to Target that partly documents what he’s been doing for the past few decades. He directed two seasons of the This American Life TV show and a behind-the-scenes documentary for Judd Apatow’s Funny People; after his career stalled out just as he moved his family to Los Angeles, he found a second life directing commercials. Between paying jobs, Wilcha tried to complete a second feature, but various follow-up documentaries stalled out due to lost momentum or funding, and the resulting hard drives of aborted projects now serve as the foundation of Flipside. The film technically centers upon the eponymous Championship Vinyl-esque record store in Pompton Lakes, NJ, where Wilcha cut his teeth as a teenager, as it struggles to keep its doors open after the arrival of Station 1, a rival record store literally two minutes away. But Flipside frequently digresses from its locus to Wilcha’s various unfinished projects on subjects like screenwriter David Milch, cult musician Uncle Floyd, the White Stripes and jazz photographer Herman Leonard. The result is an oft-moving examination of the value of labor and the struggle to complete creative work while life, family, and financial responsibilities compete for dwindling time.

Filmmaker spoke with Chris Wilcha ahead of Flipside’s North American premiere at TIFF. The film will have its U.S. premiere at DOC NYC Sunday, November 12 at the IFC Center with Wilcha in attendance. It will screen again on Wednesday, November 15^th at the Village East.

Filmmaker Magazine: I want to start with The Target Shoots First, because I watched it for the first time during the pandemic on a recommendation, and it subsequently went around some of my friends because we’re all music dorks.

Chris Wilcha: Did it feel very ’90s nostalgia?

Filmmaker: It was a combination of, “Wow, look at all the objects that populate the screen,” but also how much things haven’t changed. Columbia House is just Spotify now. But how different was the process of culling the hours of footage from the ’90s for The Target Shoots First vs. culling the hours of home video for Flipside?

Wilcha: There are absolute parallels. I am one of those people who is a collector. Some people go out, shoot their boards and come home with very modest dailies. I’m a gatherer and a marinater, meaning I have an instinct to shoot something. It’s almost like street photography, where you’re like, “I’m drawn to this, I’m interested in this person,” and you shoot and gather. That’s not to say I haven’t done things for hire where it was like, “You have this many days. You have to get in, you have to get out.” But The Target Shoots First was an astonishing pile of footage, and I was so unschooled then. I didn’t know what I was doing. So, the pleasure now is that, yes, all this material had gathered, but I had a slightly better eye to say, “Oh, that doesn’t work, but here’s the footage that’s the most alive and seems to echo with the most possibility,” so starting to organize it was a little easier. Digging through huge volumes of stuff seems to be a weird fact of my life, but I think we’re all that way! Our phones are polluted with videos and we all have hard drives full of stuff.

Filmmaker: You left Columbia Record House in ’94?

Wilcha: Around then. Then I went off to grad school.

Filmmaker: I was curious about the timeline. The movie premiered in ’99?

Wilcha: I think it was late ’99 and it mostly caught fire in 2000.

Filmmaker: So during that time you were in grad school, were you editing Target?

Wilcha: Yeah. What I would do, much like Flipside—and it’s very wise of you to have spotted some echoes because it’s almost a sequel…

Filmmaker: That’s how I’ve been describing it.

Wilcha: By the way, no one in the world was waiting for a sequel to The Target Shoots First. But for me, it is a funny echo of so many of the ideas and thoughts and theories of The Target Shoots First. What happened in grad school is I was attending class, looking at the footage. I would dub it, back it up, do string-outs of highlight reels, but I didn’t know if I was going to use it in any meaningful way. Then there came this moment when I needed to make a thesis film. One of the gifts of CalArts—a lot of my friends had gone to film schools where they say, “Only this number of people can make thesis films and everyone crews on them” or “You can only make a 15-minute thesis film.” CalArts was like, “Make whatever the fuck you want: a one-minute film, a 300-minute film, an installation…” 

So, I made a 70-minute documentary that was my thesis, and that was The Target Shoots First. It was made at CalArts, on those machines and with the help of my mentors who would watch cuts. A lot of these people were serious artists—like, for instance, James Benning. His advice to me at one point was, “Make 60 one-minute sequences,” which is so James Benning.

Filmmaker: That’s the Benning cut.

Wilcha: It was basically, “Make the structuralist version that has no narrator.” He was helpful in other ways, but that was definitely like, “I don’t think I’m going to take that note, James.” I actually love him. I just saw him a week ago. He has a new movie out. It showed at the Academy, and [with] my pal—one of my collaborators on Flipside and I, a fellow Cal Arts grad named Adam Goldman—we went to see James’ new film. It was great to see him. Everyone’s getting older now.

Filmmaker: Looking at the structure of Flipside: a lot of times with docs of this stripe, digressiveness can be a problem, but here it’s very much the point. When did the film start to take shape? Was it the second visit to the record store? And when did the idea to incorporate all the unfinished docs come?

Wilcha: So, periodically, every couple of years, I would go to Flipside and do some shooting. Some of those shoots I didn’t include, because either they didn’t yield much or didn’t have footage that was necessary to tell the story. But the original goal was, “I am going to make something about Flipside.” Time continued to pass. There came a point when my friends and family were sort of sick of me saying I was going to do this. It was a complete labor of love. So, a paying job would come and I’d go do that, or I would work with an editor and the editor would be like, “I can give you a week after I do this Chevy job,” and a week wasn’t enough time to make any meaningful progress. 

During the pandemic, there was a group of people that I am friends with and have known for a very long time. One is Joe Beshenkovsky, the editor, and he has a producer that he works with, and there was two producers that I had done a lot of commercial work named Michelle Currinder and Alex Fisch, and we had done a network documentary as a complete job for hire. We had built this machine and done something entrepreneurial, and it went well. One of the producers said, “Why don’t we make your film?” 

I had a treatment that was 30 pages long, but people would read it and be like, “I don’t… What’s it going to sound like?” To me, it was so obvious—it would have been an continuation of that Target Shoots First thing. But digressiveness is hard to capture in a treatment. So, during the pandemic, when Joe and this other editor Claire Ave’Lallemant came on board—she’s a younger editor that he works with, and we started to block things out: “I love this moment, this is a scene I really like.” But what got really tricky was making the connections. And voiceover writing for documentary is exhausting. It is so uniquely, weirdly a genre of writing unto itself. It’s like aphorisms: You can’t get too expository, you can’t crowd too much of the frame, you don’t want to say too much. So, it was just the labor of trying things. Joe, our editor, was responsible for much of the structure. He would say, “I think this would go here,” and two things that seemed unconnected suddenly connected. Then you start from building there. Once we had this proof of concept that voices could occur—that started with Herman Leonard, where he comes in the beginning and recurs about eight minutes later, and we were like, “Oh, this could work, where a voice returns.” You introduce a character, they disappear, and then you bring them back. The trigonometry of that editorial exercise took time; it was trial and error.

Filmmaker: When you were stuck in the edit of trying to get two sequences to connect, was the solution to have you jump in?

Wilcha: A danger of this documentary is, “Does anybody particularly wanna hear a middle-aged white guy’s story?” I was a little nervous about foregrounding too much of myself. So, I would sometimes focus more attention on the case studies, the mini-documentaries within the documentary. But then we shared a cut with some friends and family, and some people were like, “You’re missing. We need you to come back in this moment. You’re gone for like 12 minutes.” It was then that I felt a certain amount of freedom to say, “Okay, I’m not getting in the way. If I could find enough balance to enter and then leave, my presence will be tolerable.”

Filmmaker: I’m very curious—and I hope you don’t take the question the wrong way—were you conscious of how much your voiceover resembles Ira Glass’s?

Wilcha: I wasn’t! But listen, Ira is a massive influence on a lot of people, myself included. I worked on the television version of his radio show for a couple years and I studied what they did. That was pure grad school storytelling for me. I don’t take it as an insult. There is a genre, and now it is ubiquitous, of a kind-of NPR, thoughtful, reflective thing that he’s the godfather of. The thing about him, it’s so deceptive, right? It sounds conversational, but you can feel the writing.

Filmmaker: There’s the pregnant pauses…

Wilcha: It has such integrity, such consideration, and I learned that from him. So no insults. I wouldn’t want it to tip too far, and it is interesting that he’s in it, right? I had this funny idea the other day where I was like, “Oh, we should get him to narrate the trailer.” Then I was like, “No, that’s a bad idea,” because then it just seems like a This American Life story.

Filmmaker: I want to talk about your commercial work a little bit. Something that was very interesting to the friends of mine who saw this movie, because we know a lot of doc people, is your story is such a familiar one of starting projects and putting them away to take the paying job. The few scenes of you directing commercials in Flipside are really not unlike people directing non-fiction work. I think about you staging the scene with the vinyl in the living room, which is something a lot of doc people do in order to mold a shot. Is there any commercial work you’ve done, outside of the insurance policy one that you included in the movie, that allowed you to flex some of the skills that you had honed in your non-fiction work?

Wilcha: I have done my share of not particularly creative commercials that, as we say, I’m sure you’ve heard this phrase, [are] “for the meal, not the reel.” But every once in a while, I will get to do something that is extraordinary and very special. I got to shoot with Emmanuel Lubezki, doing an eight-minute launch film for the Apple streaming service. We interviewed directors, filmmakers, actors all working on Apple projects: Steven Spielberg, Ron Howard, Reese Witherspoon, J.J. Abrams. We were essentially making this film and I was doing exhaustive multi-hour interviews with these people, and it was slightly heartbreaking that it would never have a life beyond promoting this streaming service. But, I mean, working with Chivo—this is the greatest living cinematographer, and I only get to do that because it’s a commercial budget that would support his participation, and having him on that legitimized that job in such a huge way. They all talked in very thoughtful and reflective ways about their creativity and their creative process, and I thought we got some really great interviews. People were so excited to be shot by him. He was such a selling point for the interviewees to come in. To me, that was extraordinary, but that was a thing that nobody saw, nobody cared about, nobody wrote about. And I understand.

But there’s a lot of hackdom, I’m not going to lie—mid-level, forgettable health care, car, lifestyle stuff. Don’t get me wrong: there’s a lot of thoughtful, smart people in the world of advertising. I’ve been very lucky to make a living that way. The problem was, you get to this point where you just want to make something that has some meaning. We self-financed Flipside. Nobody paid us to do this, and it’s probably not really a viable business model. The commercial work is going to continue—that is the way I make a living. The hope and the dream, though, is to be able to make more long-form documentaries, to strike that balance again.

Filmmaker: One of the reasons a few of us connected with Target Shoots First—

Wilcha: I got to get that in the world, by the way. Because that thing does not exist in the world.

Filmmaker: What happened with it? Was it music rights?

Wilcha: No, no. Maybe it’s my own fault, if I think about it. That thing was a fluke of nature. It was my grad school thesis project, it had a lovely festival run just before the Internet. I mean, we all had AOL or whatever, but… It was licensed and broadcast on HBO for a year or two. It maybe bopped around to a couple other places. I think it had a hot minute on the Sundance Channel.

Filmmaker: That’s where a lot of people I know saw it.

Wilcha: But these were licenses, so they didn’t own it. Then there came a point when the interest waned and it had no home, and it was a weird transitional moment where DVDs were dying, and nobody was particularly motivated to make a DVD out of it, and then there just came this moment where it settled into the murk of the past. I had it on a Vimeo page for a while that I just sort of threw out there.

Filmmaker: It’s on the Internet Archive now.

Wilcha: I’ve heard. I don’t think anyone’s going to do this, but how fun would it be to sell it along with Flipside and someone sees it as like a two-for-one? But we’re nervous enough about selling Flipside, so I don’t know if I want to be like, “Hey, can you buy the cousin of this?”

Filmmaker: In Flipside, you cringe at the footage of a younger you hemming and hawing about the notion of personal integrity, but I always felt one of the worst things about my generation was how we rejected that anxiety out of hand. It’s not always about being an absolutist or “reject the paycheck,” but it’s about caring where your name is and where the money is coming from. What’s interesting about Flipside is, you channel that anxiety into exploring the value of labor, and how it only sometimes ties into personal satisfaction and creative fulfillment. When did that come into the fold, either in the edit or the writing?

Wilcha: Even back then, I was asking these questions about, how does anybody make a living doing work that is meaningful? It was an obvious question, yet somehow everyone was doing things where they seemed okay with being miserable, or selling their time and labor but carving out this other thing. I was trying to see if there was a way to make a living doing the thing you love, and it is fucking hard. I continue to grapple with this. Sometime you’re on a commercial job where you just can’t believe who you’re making propaganda for. It’s also a freelance hustle. I’m not asking for someone’s sympathy. I’ve had a good commercial directing career, but it’s nerve-wracking. You finish that job and the phone stops ringing, and all of a sudden you might not work for three weeks or three years. That gig economy still haunts me and fills me with anxiety. So, I think that’s a constant reflection on how to make things. 

What’s so tricky about Flipside is this group of people came together, but there was so much sweat equity. There was so much time that people were working where I could not pay them, and that is the most uncomfortable feeling: “Hey, you person I love who have incredible skills as a DP, as an editor, as a composer—I can’t pay what you’re worth, but will you work on this thing?” The hope, the dream, maybe the lie, is that the thing begets other things, and the hope and dream, and hopefully maybe not a lie, of Flipside is it begets more projects that we can all collaborate on and everyone could get paid their proper rate. I think you need to take those risks. Otherwise, you’re just on the commercial treadmill endlessly. Everyone took a risk on this. The editor, Joe, is a fucking unicorn. This guy is a phenomenal editor and he’s in incredible demand. He did the Kurt Cobain doc with Brett Morgan, he did Jane, he did the Garry Shandling doc with Judd Apatow, and we could not pay him his rate. But he believed in it, signed on to do it and here we are. I feel very lucky that he carried that belief.

Filmmaker: When did Apatow come on board [as a producer]? Was it after the fact?

Wilcha: Yes, but at a crucial moment. We basically propped the edit up, had a cut and knew we had a lot of work to do, but we felt like it was good enough to show someone. I had met him years before, Joe has worked with him. I also wanted to interview him because he was a part of the story of how I moved my whole family to Los Angeles at his behest and then found myself out of work with no prospects. So, I went back and interviewed him and he said, “Show me a cut.” Then he was like, “I really like this. Let’s keep talking.” At a certain point, he was like, “I want to help you guys.” But he understood that the marketplace was in the middle of collapsing; the doc gold rush of five years was over. So he basically said, “Let’s get a cut to a certain point,” then hosted a screening at his office. That was when we got some really meaningful feedback about things that were missing, or more of this and less of this. At that point we were able to see that we were on the right track. 

So, he came in pretty late, and gave us a little bit of money just to get that edit propped up, and I think it was really smart of him. He wasn’t just going to write a check and pay for it. He said to me at one point, “This isn’t, like, a Michael Jackson documentary.” There’s not star power. But so we got that edit propped up, and getting over that hump was what got us a cut worthy enough to submit to TIFF as a work-in-progress. We got accepted, which was our goal, then we had to make this mad dash sprint to finish—we had to raise money, knock on some doors and get all the music clearances. It has been the wildest summer, because all the loose ends and all the little bets we placed, we had to then cash in. So songs that just sat there where we were like, “We love this. We’ll figure this out later,” all of a sudden we were like, “Holy shit, we have to clear this.” Clearing music for documentaries is unbelievable. Terrifying.

Filmmaker: I’m really glad you got “Unsatisfied” in there. It hits like a bullet.

Wilcha: That cleared literally ten days ago. The paperwork is wet on that agreement. Seriously.

Filmmaker: What year did you do the David Milch interview?

Wilcha: We did it in early 2021, then I went back a couple months later and shot with him in his room and showed him the footage, then interviewed his wife Rita. He would get stuck—you’d talk to him, then 15 minutes would go by and he’d start to get a little agitated and focus on just one thought. We didn’t put any of that in because it seemed creepy and undignified. But he was sharp. He would say these wildly insightful things and then retreat into himself. I hope he’s okay.

Filmmaker: The actor you cast in the insurance policy commercial, was that Dan from Gimme Gimme Records?

Wilcha: Yes, Dan Cook. Love that fuckin’ guy. That’s a great record store, too.

Filmmaker: I’ve only heard stories.

Wilcha: Where are you based?

Filmmaker: I’m from Chicago, but I live in Brooklyn now.

Wilcha: Well, if you’re ever out in Highland Park—actually, he just moved the store, though I think it’s still technically Highland Park. He’s amazing. Again, I just collected those casting tapes. I ran into him at a Bill Orcutt show. I hadn’t seen him since the commercial, it had been years. I said, “Dan, you probably don’t remember me. I just made this documentary. You’re in it. Would you be able to look at this footage?” He was so cool. He was like, “Yeah, man. Just send it.” The next day, he wrote me this beautiful text that was like, “As an artist who’s had a side gig as a record store owner going on 22 years, I really identified with the film.” I didn’t realize this: His side gig was the records. That was not what he intended to do. I’m finding this out about people. That was not his entrepreneurial vision for his adult life.

Filmmaker: I’m curious about the shot where you convey the distance between the two record stores. Was that a drone?

Wilcha: Yes.

Filmmaker: What was the thinking behind that? Because relative to the rest of the film…

Wilcha: No, no, I know. I shot some things that were too fancy for the documentary. I did a voiceover read in an abandoned radio station in New Jersey, and it was too majestic. It ate the film alive. The film is a handmade collage of all this different shit. It couldn’t handle something that was too well shot. Isn’t that funny? 

But what happened is, I wanted to convey the distance between the two stores. We tried it as a whip zoom where we went from one to the other. We tried an on-the-ground gimbal shot where I walked from one store to the other, but it took too much screen time. We also had a Google Map in there, like an animation of a walk, but that also felt punted. It took us a half hour just to nail a drone shot. It was really important to show that these stores are not on other sides of town. They are two minutes as the crow flies. 

I am very drone allergic, especially in documentaries. I think they are so clichéd. It’s always the shot of the town and the wide [shot] and the establishing [shot]. There was something I love about seeing Flipside from above, then cruising over and landing at Station 1. So, yes, it was a little bit of a stylistic risk, but I felt that it carried an idea that was important. A little visual joke.

Filmmaker: It was a little surprising that you were willing to admit you sold your records at Station 1 instead of Flipside.

Wilcha: I’m a little worried that Dan [Dondiego, owner of Flipside Records] is going to be mad at me.

Filmmaker: I talked to a buddy about it and he was upfront in saying, “He does not come off well in that moment.”

Wilcha: I know, I know.

Filmmaker: But your reasoning for doing so makes sense. Was there any trepidation around including that bit?

Wilcha: I had many conceptual ideas that fell apart while I was doing this.

Filmmaker: Please tell me all of them.

Wilcha: Well, I had one where I was like, “I am going to do a conceptual thing where I sell everything at my parents’ house but I interview the people who buy it.” But that failed—people didn’t want to be interviewed, they just wanted to buy the stuff. Then I thought, “Would a conceptual idea be all the records I bought return to their motherland where they were first bought?” Which is at Flipside—literally, Dan’s handwriting is still on them. But honestly, Dan’s store is over-fucking-flowing, and I would love to see the stuff in other people’s hands. There’s something about the vitality of the way Station 1 sells things. They post it and by that afternoon it is fucking gone. That store replenishes itself constantly. He can’t keep up with his used inventory. 

This is no shade on Dan. But first, I wanted to see how much they were paying—and by the way, it turned out to be very generous—and then I also loved the idea that the stuff would find a home, that it would live on, that some younger person or collector would appreciate the artifact, even that it was sealed. I had some weird promo copies of things that are actually worth a few bucks. It was a betrayal of Dan, but I think at the end, I’m trying to remind us that Dan did something profound, and my dream for this documentary is that it finds some form of distribution where people see it and some of the cratediggers go and make the pilgrimage and spend a few bucks, and he gets a new infusion of interest. That was the goal. It couldn’t be contained in the movie. That was my thesis: “Can I help get more people in here?” That never happened during the movie, but my hope is that later, as a coda, some people just go. Imagine if someone shows up and says, “I saw the documentary. I’m spending 100 bucks.” That would be amazing.

Filmmaker: Tell me about your unfinished White Stripes documentary.

Wilcha: It’s not like somebody was funding it and it fell apart. I had a girlfriend who was working for the White Stripes, and they were in the process of catching fire. I would go to her with shows up and down the East Coast, and you’d see the reaction. They’d be backstage, just the two of them and their sound guy, and I was like, “This is the Don’t Look Back moment. They’re on that tour.” It must have been 2001. Every once in a while, I would be allowed to film. So, I would film in the photographer’s pit and get a couple of songs. Me and a friend named Sam Levy took Bolexs to Union Square Park; they played a free live show, we shot that. I’ll never forget, they had a run of shows at the Bowery Ballroom, and the celebrities started coming backstage. The Strokes started hanging out. I didn’t know Jack [White] well enough, and I could sense he was very suspicious of outsiders, but I got a bunch of songs, a bunch of footage—and then my girlfriend and I broke up. The access was gone. I still have a bunch of stuff. Maybe there will be somebody who makes the epic White Stripes doc and I’ll ship them the archival footage. I remember there was a weird thing where [Jack] let some people shoot some of those Bowery shows and I think he ended up getting into a big fight with them and suing them for the footage. He was very controlling, and brilliantly so, but it was one of those moments where a little bit more negotiation, staying in that relationship a little bit longer—it was the blow up moment. All of it was catching fire, I knew it in my gut and I missed it.

Filmmaker: What was the biggest challenge in terms of writing or editing Flipside and how did you get out of it?

Wilcha: The footage I was in, sometimes I didn’t love the way things looked or shot or even how I looked. Two people were in the trenches with me—Adam, who co-wrote it with me and also composed the music, and there was Joe, the editor. I would often lose sight of something, because I would have some visceral, vulnerable, self-loathing, insecure response to what was happening, and both of them steamrolled over me and carried me over the finish line to say, “You got to let go of that shit. Yes, that piece of voiceover is making you cringe. You know what? We have to fuckin’ rewrite it. Let’s sit here and rewrite it right now.” Because I would put things up and be like, “I hate what I’m saying.” It was just the constant revising with those two key players that got it to the point where I felt like, “Oh, we finally found my voice again,” and it took a fuckton of time to get there. There were many misfires. I was reading some review of it this morning where you can feel the tightrope walk of his criticism. A couple of bad V/O moments, and he could have hated this fuckin’ thing, and it’s a couple of V/O moments, and he likes the thing. That was the tricky razor’s edge we were walking on the whole time. It was other people being accountable to other people that got me out of bed every day to do it. I probably would have procrastinated on it even longer. I would have kicked it down the road. It was the people saying, “No, you have to show up every day to fix this thing.”